4-Hydroxybenzaldehyde → Benzaldehyde, 4-[(2-methoxyethoxy)methoxy]-

Participants

Reaction Steps

To a solution of 4-hydroxy-benzaldehyde (3.7 g, 30 mmol) and diisopropylethylamine (7.6 mL) in CH2Cl2 (60 mL) was added MEMCl (5.0 mL) in CH2Cl2 (17 mL) dropwise at 0° C. The mixture was stirred at RT for 3 h, quenched with Hcl (60 mL, 0.5 N). The mixture was extracted with CH2Cl2. The organic phase was washed with NaOH solution (1 N) and water. The separated organic phase was dried under Na2SO4, filtered and concentrated to give 6.2 g of product (97%) which was pure enough to be used to the next reaction without further purification. 1HNMR (200 MHz, CDCl3): δ 3.36 (s, 3H), 3.54 (m, 2H), 3.83 (m, 2H), 5.41 (s, 2H), 7.16 (d, J=8.7 Hz, 2H), 7.83 (d, J=8.7 Hz, 2H), 9.90 (s, 1H).

Provenance & Evidence